An andrographolide from helichrysum caespitium (DC.) sond. Ex Harv., (Asteraceae) and Its antimicrobial, antiquorum sensing, and antibiofilm potentials

Helichrysum caespititium (DC.) Sond. Ex Harv., (Asteraceae) is a medicinal plant indigenous to South Africa. Its non-polar extracts exhibit significant antimicrobial and, in particular, antigonorrheal activity. This study aimed at isolating and purifying the active antigonorrheal compound from its chloroform extract and validating its inhibition potential on quorum sensing (QS) and biofilm formation of multi-drug resistant (MDR) pathogens. Phytochemical investigation of aerial parts of H. caespititium afforded a diterpene lactone (CF6). The effect of CF6 on violacein production and biofilm formation was studied using in vitro quantitative violacein inhibition (Chromobacterium violaceum) and biofilm formation (Streptococcus pyogenes, Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Neisseria gonorrhoeae, and Pseudomonas aeruginosa). The structure of CF6 was characterized using FTIR, NMR, and UPLC-MS data accordingly, as 10-methyl-8-(propan-17-ylidene)naphthalen-9-yl)-11-vinyl- 14-hydroxyfuran-16-one. The susceptibility testing of the pathogens against CF6 revealed Neisseria gonorrhoeae was noticeably susceptible with a MIC value of 60 g/mL, while Streptococcus pyogenes and Staphylococcus aureus showed MIC of 125 g/mL. All gram-negative pathogens, Escherichia coli, Klebsiella pneumonia and Pseudomonas aeruginosa were inhibited at 250 g/mL. CF6 also inhibited the production of violacein by 51.88% at 250 g/mL and prevented cell attachment by 40.76–81.18%, with N. gonorrhoeae being highly prohibited from forming biofilm. In conclusion, 10-methyl-8-(propan-17- ylidene)naphthalen-9-yl)-11-vinyl-14-hydroxyfuran-16-one is the first of its kind to be isolated from the non-polar (chloroform) extract of South African Helichrysum caespititium with antigonorrheal, antimicrobial, antiquorum sensing, and antibiofilm properties. The compound may serve as a drug candidate against MDR pathogens.SUPPLEMENTARY MATERIAL : FIGURE S1: The proton (1H NMR) spectrum of CF6. FIGURE S2: The carbon-13 (13CNMR) spectrum of CF6. FIGURE S3: Correlation spectroscopy (COSY) spectrum of CF6. FIGURE S4: Attached proton test (ATP) spectrum of CF6. FIGURE S5: Heteronuclear Single Quantum Coherence (HSQC) spectrum of CF6. FIGURE S6: Heteronuclear multiple bond correlation (HMBC) spectrum of CF6 and FIGURE S7: High resolution electrospray ionization mass spectrometry (HRESIMS) spectrum of CF6.The South African National Research Foundation (NRF) Thuthuka Grant, South African Medical Research Council–Self Initiated Research (SAMRC-SIR), and Sefako Makgatho Health Sciences University Research and Development Grant.https://www.mdpi.com/journal/biologyam2022BiochemistryGeneticsMicrobiology and Plant Patholog

An Andrographolide from Helichrysum caespitium (DC.) Sond. Ex Harv., (Asteraceae) and Its Antimicrobial, Antiquorum Sensing, and Antibiofilm Potentials

Helichrysum caespititium (DC.) Sond. Ex Harv., (Asteraceae) is a medicinal plant indigenous to South Africa. Its non-polar extracts exhibit significant antimicrobial and, in particular, antigonorrheal activity. This study aimed at isolating and purifying the active antigonorrheal compound from its chloroform extract and validating its inhibition potential on quorum sensing (QS) and biofilm formation of multi-drug resistant (MDR) pathogens. Phytochemical investigation of aerial parts of H. caespititium afforded a diterpene lactone (CF6). The effect of CF6 on violacein production and biofilm formation was studied using in vitro quantitative violacein inhibition (Chromobacterium violaceum) and biofilm formation (Streptococcus pyogenes, Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Neisseria gonorrhoeae, and Pseudomonas aeruginosa). The structure of CF6 was characterized using FTIR, NMR, and UPLC-MS data accordingly, as 10-methyl-8-(propan-17-ylidene)naphthalen-9-yl)-11-vinyl-14-hydroxyfuran-16-one. The susceptibility testing of the pathogens against CF6 revealed Neisseria gonorrhoeae was noticeably susceptible with a MIC value of 60 µg/mL, while Streptococcus pyogenes and Staphylococcus aureus showed MIC of 125 µg/mL. All gram-negative pathogens, Escherichia coli, Klebsiella pneumonia and Pseudomonas aeruginosa were inhibited at 250 µg/mL. CF6 also inhibited the production of violacein by 51.88% at 250 µg/mL and prevented cell attachment by 40.76–81.18%, with N. gonorrhoeae being highly prohibited from forming biofilm. In conclusion, 10-methyl-8-(propan-17-ylidene)naphthalen-9-yl)-11-vinyl-14-hydroxyfuran-16-one is the first of its kind to be isolated from the non-polar (chloroform) extract of South African Helichrysum caespititium with antigonorrheal, antimicrobial, antiquorum sensing, and antibiofilm properties. The compound may serve as a drug candidate against MDR pathogens

Antiuropathogenic and antioxidant activities of Hypoxis hemerocallidea Lam. extracts, and compounds from its taxonomically related species

Hypoxis hemerocallidea Lam is one of the 43 Hypoxis species in South Africa, marketed extensively as over the counter herbal product for the management of several diseases. The plant commercial products link efficacy to hypoxoside 4, its aglycone (rooperol), or β-sitosterol. This study investigated antibacterial and anti-oxidant activities of four other molecules and two extracts from the Hypoxis plant. Visual antioxidant limit of detection and free radical scavenging activities of test samples were determined using 20 mM hydrogen peroxide, 0.4 mM DPPH or ferric reducing antioxidant power assay. Quantitative free radical was determine by spectrophotometric method while antibacterial activity was evaluated using MICs against uropathogens: S. aureus (ATCC25923), S. marcescens (ATCC 14041), P. aeruginosa (ATCC 9721), P. mirabilis (ATCC 33583) and E. coli (ATCC 10536). Anti-oxidant activities visual limit of detection of 0.06 mg/mL and percentage free radical scavenging activity (IC50 = 0.048 - 0.032 mg/ml) for pure compounds 1 - 4 and (IC50 = 0.037 - 0.039 mg/ml) for extracts were obtained. The reducing power IC50 ranged between 0.15 - 0.23 mg/ml for extracts and 0.11-0.35 mg/ml for standards. Antibacterial potentials show a noteworthy to moderate MIC values of 0.20 - 1.56 mg/ml against S. aureus (ATCC 25923), S. marcescens (ATCC 14041), P. aeruginosa (ATCC 9721), P. mirabilis (ATCC 33583) and E. coli (ATCC 10536). Galpinoside 5, hemerocalloside 3 and curculigoside C 2 are the other active compounds in Hypoxis plant

Antioxidant and Antimicrobial Evaluations of <i>Moringa oleifera</i> Lam Leaves Extract and Isolated Compounds

Moringa oleifera, native to India, grows in tropical and subtropical regions around the world and has valuable pharmacological properties such as anti-asthmatic, anti-diabetic, anti-inflammatory, anti-infertility, anti-cancer, anti-microbial, antioxidant, and many more. The purpose of this study was to assess the free radical scavenging ability of two extracts and two pure compounds of M. oleifera Lam (hexane, ethanol, compound E3, and compound Ra) against reactive oxygen species, as well as their reducing power and antimicrobial activities. Bioautography antioxidant assay, 2,2-diphenyl-1-picrylhydrazyl (DPPH), hydrogen peroxide (H2O2) free radical scavenging, and iron (iii) (Fe3+ to Fe2+) chloride reducing power assays were used to assess the extracts’ qualitative and quantitative free radical scavenging activities. Furthermore, the extract and the compounds were tested against both Gram-positive and Gram-negative bacterial strains suspended in Mueller–Hinton Broth. The extracts and pure compounds showed noteworthy antioxidant potential, with positive compound bands in the Rf range of 0.05–0.89. DPPH), H2O2, and Fe3+ to Fe2+ reduction assays revealed that ethanol extract has a high antioxidant potential, followed by compound E3, compound Ra, and finally hexane extract. Using regression analysis, the half maximal inhibitory concentration (IC50) values for test and control samples were calculated. Compound Ra and ethanol exhibited high antioxidant activity at concentrations as low as ≈0.28 mg/mL in comparison with n-hexane extract, compound E3, ascorbic acid, and butylated hydroxytoluene standards. The radical scavenging activity of almost all M. oleifera plant extracts against DPPH was observed at 0.28 mg/mL; however, the highest activity was observed at the same concentration for ascorbic acid and butylated hydroxytoluene (BHT) with a low IC50 value of 0.08 mg/mL and compound Ra and ethanol with a low IC50 of 0.4 mg/mL, respectively. The extracts and pure compounds of M. oleifera have little to no antibacterial potential. M. oleifera extracts contain antioxidant agents efficient to alleviate degenerative conditions such as cancer and cardiovascular disease but have little activity against infectious diseases

Chemical Characterization and Nutritional Markers of South African <i>Moringa oleifera</i> Seed Oils

Moringa oleifera Lam (syn. M. ptreygosperma Gaertn.) leaves are globally acclaimed for their nutritional content and mitigation of malnutrition. In most impoverished rural communities including Limpopo, Mpumalanga and KwaZulu Natal of South Africa, powdered leaves of Moringa oleifera are applied as a nutritional supplement for readily available food such as porridge for malnourished children and even breast-feeding mothers. Widely practiced and admired is also the use of the plant seed in the do-it-yourself purification of water by rural South Africans. This study aimed at identifying the chemical and nutritional marker compounds present in South African Moringa oleifera seed oils using high resolution 1-2-dimension gas chromatography in order to give scientific validation to its uses in cosmetics and particularly in culinary practices. Results obtained from two-dimension tandem mass spectrometry chemical signature revealed over 250 compounds, five times more than those reported from one-dimension gas chromatography. Whereas previous reports from gas chromatography-mass spectrometry analysis reported oleic acid (70–78%) as the major compound from oil samples from other countries, M. oleifera seed oil from South Africa is marked by cis-13-octadeaconic acid with 78.62% and 41.9% as the predominant monounsaturated fatty acid in the hexane and dichloromethane extracts respectively. This was followed by cis-vaccenic acid, an isomer of oleic acid at 51% in the acetone extract, 9-octadecanoic acid-(z)-methyl ester at 39.18%, 21.34% and 10.06% in dichloromethane, hexane and acetone extracts respectively. However, a principal component analysis with R2 = 0.98 of the two-dimension tandem mass spectrometry cum chemometric analysis indicated n-hexadecanoic acid, oleic acid, 9-octadecanoic acid-(z)-methyl ester and cis-vaccenic acid with a probability of 0.96, 0.88, 0.80 and 0.79 respectively as the marker compounds that should be used for the quality control of moringa seed oils from South Africa. This study demonstrates that South African Moringa oleifera oils contain C-18 monounsaturated fatty acids similar to oils from Egypt (76.2%), Thailand (71.6%) and Pakistan (78.5%) just to mention but a few. These fatty acids are sunflower and olive oil type-compounds and therefore place moringa seed oil for consideration as a cooking oil amongst its other uses

Phytochemical Screening, Antioxidant and Antibacterial Properties of Extracts of Viscum continuum E. Mey. Ex Sprague, a South African Mistletoe

Viscum continuum E. Mey. Ex Sprague is a woody evergreen semi-parasitic shrub that grows on the branches of other trees. It is used by African traditional healers for post-stroke management. This study reports on the qualitative phytochemical screening and the antioxidant and antimicrobial activities of Viscum continuum&rsquo;s acetone, methanol, hexane and dichloromethane extracts. Standard protocols for the phytochemical screening of extracts were employed. TLC bio-autography was used for qualitative antioxidants analysis. Assays: 2,2-diphenyl-1-picrylhydrazyl, H2O2 free-radical scavenging and ferric chloride reducing power were carried out for quantitative antioxidant analysis. The antimicrobial potential of extracts was screened using disc diffusion, bio-autography and broth micro-dilution. The results indicate the presence of alkaloids, phenolics and tannins in all extracts. Acetone and methanol revealed significant amount of saponins, phenolics, tannins and terpenoids. The extracts exhibited significant antioxidant potential on TLC with positive compound bands at an Rf range of 0.05&ndash;0.89. DPPH, H2O2 and the reduction of Fe3+ to Fe2+ assays indicated that methanol extract has a strong antioxidant potential, followed by acetone, DCM and lastly hexane. The extracts of Viscum continuum show the potential to be antibacterial agents. It can be concluded that Viscum continuum extracts contain phytochemicals which are capable of mitigating against chronic health conditions such as cancer, stroke and stress-related and infectious diseases

Current Advances in Specialised Niosomal Drug Delivery: Manufacture, Characterization and Drug Delivery Applications

Development of nanomaterials for drug delivery has received considerable attention due to their potential for achieving on-target delivery to the diseased area while the surrounding healthy tissue is spared. Safe and efficiently delivered payloads have always been a challenge in pharmaceutics. Niosomes are self-assembled vesicular nanocarriers formed by hydration of a non-ionic surfactant, cholesterol or other molecules that combine to form a versatile drug delivery system with a variety of applications ranging from topical delivery to targeted delivery. Niosomes have advantages similar to those of liposomes with regards to their ability to incorporate both hydrophilic and hydrophobic payloads. Moreover, niosomes have simple manufacturing methods, low production cost and exhibit extended stability, consequently overcoming the major drawbacks associated with liposomes. This review provides a comprehensive summary of niosomal research to date, including the types of niosomes and critical material attributes (CMA) and critical process parameters (CPP) of niosomes and their effects on the critical quality attributes (CQA) of the technology. Furthermore, physical characterisation techniques of niosomes are provided. The review then highlights recent applications of specialised niosomes in drug delivery. Finally, limitations and prospects for this technology are discussed